How to Wear Skirts Without Looking Frumpy (with 3 printable PDF guides)

by | Outfit Ideas for Specific Clothing Items, Outfit Ideas: How to Mix & Match Your Clothes | 2 comments



Skirts are wonderful for all seasons. Paired with tees in the spring/summer and boots in the winter, they make for an easy mom outfit all year round!

But there are certain fashion pauxs associated with wearing skirts that you want to avoid. My hope is to lay out some basic rules that will insure you look beautiful and not frumpy every time you pull a skirt on! 

I was feeling the third-trimester pregnancy sleepies when I snapped the photos for this post, and it kind of shows on my face! Maybe I should have just taken a nap instead 😉 But believe it or not I am SO excited to share everything that I’ve learned about styling skirts correctly! 

Here’s how we mamas can look our very best in any kind of skirt!

Balancing Proportions: Skirt Length

What skirt lengths look good on your will largely depend on your height. Tall ladies can wear most lengths. Average height ladies may need to avoid midi (calf-length) skirts but can wear other lengths. Petite ladies are most flattered in either mini skirts or long maxi skirts (to elongate their frame).

Midi length skirts (calf-length) should either be worn with shirts that are defined at the waist or tucked in (and optionally belted). Alternatively, one can hem a midi skirt to end at or above the knee. 

I’m 5’6″ and midi skirts tend to look awkward on me. An exception might be a midi pencil skirt worn with heels, but I have yet to try one. 

In the outfit below this lovely summer skirt looks awkward at it’s usual length. 

Because it has an elastic waistline, I simply rolled it a few times to shorten the skirt. Alternatively, you could hem your skirt. Voila! Balance!

Balancing Proportions: Skirt volume

If you’re wearing volume on the bottom you want to counter that with less volume on the top. Defining the waist is important when it comes to long or full skirts. Otherwise the combined loose top and skirt make you look wide and frumpy because you’ve lost your curves.

If you’re wearing a shaped skirt or mini skirt, you can sometimes get away with a loose-fitting top. However, you always want to at least partially tuck loose fitting tops so they don’t run over the skirt. 

The outfit below has a baggy, shapeless look because I paired a flowy top with a flowy, midi-length skirt.

The outfit below is also missing shape. It’s not terrible, but could be improved.

Option 1 for Balancing Skirt Proportions

Wear a fitted top. Being preggers, this is the only option of 3 that I can personally demonstrate today. 🙂 See how simply wearing a fitted tee with these skirts helps balance the proportions of a fuller skirt and a long maxi skirt? 

Option 2 for Balancing Skirt Proportions

Tuck your top. Because ma’ belly doesn’t allow for tucking right now, see an excellent example of this at the lovely “Always Amber” blog.

Option 3 for Balancing Skirt Proportions

Wear a shorter top. I don’t mean midriff! You don’t need to show skin to get the benefits of a cropped top: namely a good balance with your long or full skirt. Simply wear a shirt that is fitted and ends about where your skirt waistline starts. Or tie a knot into the shirt to bring it up to the skirt’s waistline. 

Option 4 for Balancing Skirt Proportions

Pair a loose top with a fitted skirt or mini skirt. The low volume of shaped skirts like pencil skirts and short skirts like mini skirts balance the higher volume of a loose or baggy top. The key with this pairing is to either partially or fully tuck the top so that your waist is still defined. 

The infographic in the summary section below helps illustrate Options 2-4.


What Shoes to Wear: Heels, Flats and In Between

The quick rule of thumb is to shorten the shoe height as you increase the skirt length.

But of course there are exceptions to the rule. Here’s a guide laying out all the best shoes to pair with the four most common skirt types: mini, knee-length, midi and maxi.


Leggings: How to pair them correctly

A couple common mistakes when it comes to leggings is wearing them under midi or knee-length skirts and/or wearing them without boots. They tend to drag the whole outfit down, often creating a frumpy look when not paired correctly. Read on for your three options when it comes to leggings.

Leggings in the outfit below tend to weigh it down and look awkward.

Option 1 for Leggings with Skirts

Lose the leggings.

Option 2 for Leggings with Skirts

Wear boots over leggings in the fall/winter.

The outfits below look more balanced, fresh and stylishly appropriate.

Option 3 for Leggings with Skirts

Leggings under mini skirt. 

I don’t currently own a mini skirt to illustrate Option 3, but I put together an infographic to illustrate all three options for leggings.

Infographic: Guide to Leggings & Skirts


Are you looking for more easy mom outfits & tips? 

Mom Outfits: How to Not Look Like a Frumpy Mom (Fall/Winter Edition)
Nursing Friendly Fashion: The Best Nursing Bras & Gear
Postpartum Fashion Ideas: How to Shop When Losing Baby Weight

How to Wear A Dress or Skirt in Winter to Stay Warm + Stylish

Here’s a summary of my tips for styling skirts and dresses specifically for cold weather.

Easiest types of dresses/skirts to style in winter:

  • Styles: Maxi skirt, Skater style or mini skirt, Pencil skirt (thick ponte knit), Sweater dresses, Pleated/full skirts

  • Patterns: Plaid, Dark florals

  • Fabrics: Thick materials, Corduroy, Velvet, Suede, Faux leather

Types of completer pieces to wear with dresses/skirts

  • Long duster cardigans that almost match up with the length of your skirt

  • Short, cropped cardigans for dresses or when wearing skirt with shirt tucked

  • Fitted cardigans that match the length of your top untucked or hit at a thirds ratio with a dress

  • Fitted vests (quilted vests, denim vests, fur vests)

  • Moto jackets (suede or leather)

Shoes to wear with dresses/skirts (by skirt length)

  • Knee-length or mini:

    • Hiking boots with wool socks peeking from the top + tights or leggings

    • Riding/tall boots + tights or leggings

    • Over-the-knee boots + tights or leggings

    • Ankle boots (works best with black boots + black tights or leggings)

    • Slip-on or Lace-Up Sneakers (NOT athletic sneakers) + bare legs or leggings

    • Ballet Flats + tights or leggings

  • Midi/tea length (generally tough to make it look right with calf-length dresses, but I did pin some pictures of that too!)

    • Ankle boots (bare legs or black boots + black tights)

    • Slip-on or Lace-Up Sneakers (NOT athletic sneakers) + bare legs or leggings

    • Ballet Flats + bare legs, tights or leggings

  • Maxi/floor length

    • Hiking boots with wool socks peeking from the top + tights or leggings

    • Riding/tall boots + tights or leggings

    • Over-the-knee boots + tights or leggings

    • Ankle boots (works best with black boots + black tights or leggings)

    • Slip-on or Lace-Up Sneakers (NOT athletic sneakers) + bare legs or leggings

    • Ballet Flats + tights or leggings

Accessories to Wear with Skirts/Dresses in Winter

  • Neutral or dark color, fleece-lined leggings (black, navy, gray, olive, burgundy)

  • Black fleece-lined tights

  • Belts (over dresses; at waist with shirt tucked into skirt)

  • Scarves (solid scarves, plaid scarves, animal print scarves, infinity or blanket, thick knit)

  • Statement necklaces (over a fitted long-sleeve shirt tucked into skirt)

How to layer a dress to stay warm:

  • Start with thermals underneath (my recommendation in the Layering section above)

  • Add fleece-lined tights or leggings.

  • Add a sweater dress OR a thinner dress paired with a fitted cardigan of the same length or waist length.

  • At home you can wear the “rolled wool socks” look I demonstrate in an outfit or two below. Tights and cute slippers are also a cute, comfy look at home.

  • To go out:

    • Add a vest (optional)

    • Add a long heavy coat.

    • See above for tips on which shoes to wear out.

Tips to Avoid Frumpy When Wearing Skirts/Dresses in Cold Weather

  • Wear pieces that are “in style” and not dated. Or if you have something older, try styling it with a trendier item. See the Pinterest board for “on-trend” examples.

  • Pay attention to proportions: uneven “Golden Mean” ratios work best (see this video for explanation)

  • Contrast fit: flowy skirts with fitted tops; fitted skirts with fitted tops; or fitted skirts with flowy tops

  • Wear your skirts high on your waist and wear with a fitted shirt or sweater fully tucked in. (This is great to hide the postpartum pooch but is also a trendy way to dress!)

Additional Resources for Styling Skirts & Dresses in Winter:

 Click for my pinterest board on styling skirts and dresses in cold weather

Click for my Pinterest board on styling skirts and dresses in cold weather

In Summary: How to Wear Skirts Without Looking Frumpy

Phew! That was a lot to take in! Here’s what I talked about in summary.

Balancing proportions is key when it comes to styling your skirts. Flowy or long skirts generally look best with fitted tops. Shaped or mini skirts can be paired with either fitted tops or a looser top.

And when it comes to leggings, avoid them unless wearing them with boots or a mini skirt!

This infographic pulls it all together! 

Don’t forget to download these printables to keep as reference.


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